N-(benzyloxycarbonyl)-D-γ-methyleneglutamic acid α-methyl ester

Base Information

• Chemical Name: N-(benzyloxycarbonyl)-D-γ-methyleneglutamic acid α-methyl ester
• CAS No.: 80954-41-2
• Molecular Formula: C₁₅H₁₇NO₆
• Molecular Weight: 307.303
• Mol file: 80954-41-2.mol

Synonyms:N-(benzyloxycarbonyl)-D-γ-methyleneglutamic acid α-methyl ester

Chemical Property of N-(benzyloxycarbonyl)-D-γ-methyleneglutamic acid α-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(benzyloxycarbonyl)-D-γ-methyleneglutamic acid α-methyl ester

There total 5 articles about N-(benzyloxycarbonyl)-D-γ-methyleneglutamic acid α-methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

(R)-2-Benzyloxycarbonylamino-4,4-dicarboxy-5-morpholin-4-yl-pentanoic acid methyl ester; compound with trifluoro-acetic acid (80954-44-5) → N-(benzyloxycarbonyl)-D-γ-methyleneglutamic acid α-methyl ester (80954-41-2)

Guidance literature:

With N,N-dimethyl-formamide; In water; Ambient temperature;

DOI:10.1021/jo00349a003

Reference yield: 74.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + N-(benzyloxycarbonyl)-D-γ-carboxyglutamic acid α-methyl ester (80954-39-8) → N-(benzyloxycarbonyl)-D-γ-methyleneglutamic acid α-methyl ester (80954-41-2)

Guidance literature:

With dimethyl amine; In [D₃]acetonitrile; water; for 6h; Ambient temperature;

DOI:10.1021/jo00349a003

Reference yield:

N-(benzyloxycarbonyl)-γ,γ-di-tert-butyl-D-γ-carboxyglutamic acid (56877-43-1,60686-52-4) → N-(benzyloxycarbonyl)-D-γ-methyleneglutamic acid α-methyl ester (80954-41-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) cesium carbonate / 1.) methanol, 1 h, 2.) DMF, 2 h

2: 80 percent / aq. TFA / 2 h / Ambient temperature

3: 83 percent / H₂O / 1 h / pH 4.5

4: 89 percent / DMF / H₂O / Ambient temperature

With caesium carbonate; N,N-dimethyl-formamide; trifluoroacetic acid; In water;

DOI:10.1021/jo00349a003

upstream raw materials:

formaldehyd

N-(benzyloxycarbonyl)-D-γ-carboxyglutamic acid α-methyl ester

(R)-2-Benzyloxycarbonylamino-4,4-dicarboxy-5-morpholin-4-yl-pentanoic acid methyl ester; compound with trifluoro-acetic acid

N-(benzyloxycarbonyl)-γ,γ-di-tert-butyl-D-γ-carboxyglutamic acid